Stiff Sentencing For A Young Man

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Ellis was wise enough now to know that she wanted to put that, that huge thing of hers that had just popped off in his mouth, she wanted to put it in his butt. He was wise enough now to know that he couldn't disobey her either. It would be smarter to follow her orders. Ellis told her that he understand.

Tess shuffled to her knees, "We'll get into my favorite position. I want you to get on your hands and knees. Stick your butt up and try to spread those cheeks as much as you can. Go on then." She told him.

Ellis did just ass he said. Looking at that cute little hole of his, Tess' cock was as hard as it had ever been. It was one sweet peach and Tess was one hell of a messy eater, she thought. Tess grabbed Ellis' butt cheeks with her big paws and spread them further. She thought she could see the pink little wrinkled hole wince. Tess moved her head closer, inhaling deeply and working up a big glob of spit. She dropped the spit onto Ellis' little honey hole and smiled at her handiwork.

Tess pushed the massive head of her cock between Ellis' tight cheeks. Ellis felt her apply pressure to his little opening. The pain was intense. He grunted, then gritted his teeth. Tess moaned as the giant head finally popped past his sphincter into his tight cavern. It felt like the tightest ass that Tess had ever sampled. She tried to push more of her cock inside him.

Ellis couldn't take the pain. He thought he might pass out. Ellis started to squirm and Tess responded by pushing her meaty forearm down on his neck.

"Oh fuck. You're crazy if you think you're taking this little butt away from me." She gloated.

Ellis groaned as more of her cock started to disappear into his opening. His ass clamped down on the huge phallus. "Don't fight this. You can't win. This is mine now. This sweet little sugary hole. Give it to me. Give this peach to me!" She moaned as her hips started to thrust, sending the thick shaft in and out of his ass.

The hot member scared Ellis. He didn't know what it would do next. He was so open to Tess. She was using him and enjoying him. Did his hard cock mean that he enjoyed it too? It was too painful, he thought.

Tess' big fingers dug into his ass cheeks, she was thrusting now. Sending her large shaft in and out of him with some force. She was unable to contain herself, vocally, physically, or mentally. It just felt so fucking good, she thought. Tess wrapped her body around him, her hands and knees on the dirt floor now. Anyone looking in would just see a giant thrusting ass.

Tess was breathing hot air which bathed over Ellis. He grunted along with her, his arms weak and feeling like they could give out. The horrible pain started to subside somewhat. He hadn't gone numb but that nasty stinging feeling wasn't controlling him anymore. He had to admit that Tess' complete and absolute lust was a turn on.

Tess' thrusting became more impatient. She was hammering her hard cock in and out of him and loving every minute of it. She couldn't hold back anymore and thrust so hard that it sent Ellis' head into the dirt. She collapsed on top of him and wildly smashed her oversized cock into him. Her big balls slapped against his ass and thighs.

She held him tightly against the dirt. They were both panting heavily and sweaty all over. She gave a strangled cry before Ellis felt her cock shoot inside him. Ropes of the same sticky cream which had covered his face were now painting his insides. It filled his sensitive hole. Tess wouldn't give up her thrusting and continued as the last drops finally spilled out inside him.

"...So tight..." She struggled to utter the words with heavy breaths. Her big lips starting kissing his head, neck and back. She gave his ass a light tap with her hand, "...Thanks for that too, sweet cheeks. That was so good. I haven't felt that for... in... I don't know... fuck."

Ellis smiled weakly from his position under her. Their bodies were both covered in sweat and dirt. His ass was aching as Tess finally pulled her shriveling cock from its depths. Tess pulled her body off of him as well. He suddenly felt cold and empty. Tess stood up on rubbery legs. Ellis couldn't do the same after his anal fucking so he latched onto her leg.

He told her not to move away like she had after he sucked her off. He didn't want her to leave him there in the dirt alone. She sat back down with him. He crawled into her arms, pressing against her warm body.

"This is better," he murmured.

"We still have a little more than ten hours left I think," she paused, her hand running down his spine, one of her big fingers tracing the line of his abused crack, "I was bluffing earlier. I can't actually make this time last an eternity." She said solemnly, hugging him closely.

He looked up into his arms, "Then I won't go. I don't care, they can throw down more thugs for sentencing and I'll just stay here."

She chuckled, "These people wouldn't go for that. I know after what they did to my people. Let's enjoy tonight and worry in the morning about this. I don't want this sweet little hole of yours to go to waste." Tess pressed the big finger against his asshole.

"I can't go home tomorrow. I can't." He told her, beginning to tear up, for a much different reason than he had earlier that night, he pressed his face into the shemales giant breasts.

"There's a possibility you could help me escape. Let's leave the thinking for later. For now, I've got a new position for us." She smiled down at his head, nestled between her breasts where it belonged.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
13 Comments
smoothed273smoothed273about 2 months ago

👍👍👍👍👍💖💖💖✌🙏

AnonymousAnonymous7 months ago

Well, he seems to have given her carte blanche to do whatever she wants. The (male) author likes Amazon women, but dies he also have a homosexual tendency? He has written he gave a blowjod and anal sex. Fine for a submissive lifestyle and I hope the giantess smothers him just before she uses his arm as a dildo just to enjoy DP.

AnonymousAnonymousabout 3 years ago
So sad!(

The end is so sad! I hope they will be together forever!!

Also hope the author is okay, he had not written anything for a long time.

zzingo99zzingo99about 4 years ago
Nice

Read a couple of your stories, very hot :)

braandknickersbraandknickersalmost 9 years ago
Kept me hard from start to finish

Amazing story that still has me hard. I would expect many more positions and even release for Ellis. I've read some of your other stories and always enjoy them, no different with this one except that I still remain hard. Thank You!

Show More
Share this Story

Similar Stories

The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
Tortured by the T-Girl Tutor His world turned upside down and his ass inside out.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
The Big Horny T-Girl Bodyguard She makes a deal with a bullied classmate.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
More Stories